Host-guest complexes based on calixarenes and neutral and ionic molecular guests as well as with metal ions have been investigated in solid and solution studies (C. D. Gutsehe, Calixarenes Revisited, first ed. Royal Society of Chemistry, The Cambridge, 1989; V. Bohmer, Angew. Chem., Int. Ed. Engl. 34 (1995), 713-745). As a class of materials, calixarenes form the key component for selective electrodes and membranes, chemical and biochemical sensors, and selective extraction of ions and neutral molecules (W. F. Nijenhuis, E. G. Buitenhuis, F. De Jong, E. J. R. Sudholter, D. N. Reinhoudt, J. Am. Chem. Soc 113 (1991) 7963-7968; D. Diamond, M. A. McKervey, Chem. Soc. Rev. 25 (1996) 15-24; K. B. Crawford, M. B. Goldfinger, T. M. Swager, J. Am. Chem. Soc 120 (1998) 5187-5192; S. I. Kim, T. J. Shin, M. Ree, G. T. Hwang, B. H. Kim, H. Han, J. Seo, J. Polym. Sci, Part A: Polym. Chem. 37 (1999) 2013-2026 and E. Malinowska, L. Gawart, P. Parzuchowski, G. Rokicki, Z. Brzozka, Anal. Chirsi, Acta 421 (2000) 93-101). D. S. Guo, S. Chen, H. Qian, H. Q. Zhang, Y. Lui, Chem. Commun. 46 (2010) 2620-2622 report of a main chain supramolecular polymer where the dynamic bonds are those supramolecular interactions between a bis-p-sulphonatocalix[4]arene and an electro-responsive bis-viologen. The viologen, in its oxidized state, binds to the calixarene moieties but does not interact as strongly with the negatively charged calixarenes in its reduced neutral state.
There have been reports focused on covalently bound calixarene main chain polymers (G. Uysal, et al., Synthesis and binding properties of polymeric calix [4] arene nitriles, Reactive and Functional Polymers 50 (2002) 77-84; A. Katz, et al., The First Single-Step Immobilization of a Calix-[4]-arene onto the Surface of Silica, Chemistry of Materials 14 (2002) 3364-3368; S. D. Alexandratos et al, Synthesis and Ion-Binding Affinities of Calix[4]arenes Immobilized on Cross-Linked Polystyrene, Macromolecules 34 (2000) 206-210; C. W. Hall, J. S. et al., Clean and efficient syntheses of calix[4]arene modified polymer supports, Green Chemistry 3 (2001) 114-122; K. Ohto, et al., Adsorptive Separation of Lead and Zinc Ions by Novel Type of Calix[4]arene Carboxylate Resin Immobilized with Polyallylamine, Chemistry Letters 26 (1997) 647-648; S. Shinkai et al., Selective adsorption of UO22+ to a polymer resin immobilizing calixarene-based uranophiles, Journal of Polymer Science Part C: Polymer Letters 26 (1988) 391-396; L.-Z. Meng, et al, Preparation and behavior of calix[4]arene-containing organosilicone resins (I), Journal of Applied Polymer Science 80 (2001) 58-64; A. Yilmaz, et al, Synthesis and binding properties of calix[4]arene telomers, Journal of Polymer Science Part A: Polymer Chemistry 37 (1999) 4351-4355; M. T, Blanda, et al., Syntheses and characterizations of two copolymers containing cone conformations of calix[4]arenes in the polymer backbone, Chemical Communications (1998) 139-140; Z.-L. Zhong, et al., Synthesis and properties of calixcrown telomers, Journal of the Chemical Society, Chemical Communications (1995) 1737-1738; P. Parzuchowski, et al, Calix[4]arene derived tetraester receptors modified at their wide rim by polymerizable groups, New Journal of Chemistry 23 (1999) 757-763; M. T. Blanda, E. et al., Syntheses and characterizations of three vinyl copolymers containing pendant calix[4]arenes, Polymer 39 (1998) 3821-3826; D. M. Gravett, et al, Synthesis and Photophysical Properties of a Novel Water-Soluble, Calixarene-Containing Polymer, Macromolecules 29 (1996) 617-624; and S. J. Harris, et al., Polymeric calixarenes. Synthesis, polymerisation and Na+ complexation of a calix[4]arene methacrylate, Journal of the Chemical Society, Chemical Communications (1991) 1224-1225.)
The references cited herein are hereby expressly incorporated by reference as fully as if their content had been set forth herein.
No report has focused on a sulfonated calixarene unit immobilized as a pendant electrochemically-responsive system on a polystyrene backbone.
There is a need to provide polymeric styrene based materials for reversibly binding materials.
A styrene-based polymer with pendant sulfonated calixarene has been synthesized. The polymer is sensitive to electrical stimuli as determined by its ability to reversibly bind a guest molecule.